New synthesis of 2-aryl-3-substituted benzo [b] furans from benzyl 2-halophenyl ethers

…, D Miguel, A Martínez, A Pérez

Index: Sanz, Roberto; Miguel, Delia; Martinez, Alberto; Perez, Antonio Journal of Organic Chemistry, 2006 , vol. 71, # 10 p. 4024 - 4027

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Citation Number: 28

Abstract

Treatment of benzyl 2-halophenyl ethers with 3 equiv of t-BuLi results in Li-halogen exchange and lithiation at benzylic methylene simultaneously. These dianions do not undergo Wittig rearrangement and can be trapped with electrophiles. Their reactions with carboxylic esters afford the corresponding 2-aryl-3-hydroxy-2, 3-dihydrobenzo [b] furans as a mixture of diastereoisomers. Subsequent acid-catalyzed or mediated dehydration gives ...